Antioxidant



Patented July so, 1935 York, N. Y.,, a

10 Claims. (01. 18-50) duly rapid deterioration due to oxidation and the like.

This invention, in brief, consists in treating the rubber or other like organic material with a member of a class of compounds which may be designated as diamino diaryl alkanes, in which the two aryl groups are attached to different carbon atoms of an aliphatic nucleus. They have the general structural formula wherein A and A represent amino groups, X represents an aliphatic nucleus, and R and R represent aromatic nuclei attached to different carbon atoms of the nucleus X. The amino groups A and A may be either primary, secondary, or tertiary and may contain any hydrocarbon substituents such as alkyl, aryl or aralkyl groups.

For example, the following compounds are typical members of the class of anti-oxidants described above: p,p diamino dibenzyl; p,p'di- (methylamino) dibenzyl; p,p di(ethylamino) dibenzyl; p,p' di(butylamino) dibenzyl; p,p' di- (benzylamino) dibenzyl; p,p dianilino dibenzyl; p.10 di(p-tolylamino) dibenzyl; p,p di(naphthylamino) dibenzyl; p,p' diamino diphenyl 1,2 propane; p,p' diamino diphenyl 1,3 propane; p,p' diamino diphenyl 1,3 isobutane; p,p' diamino di-otolyl 1,2 ethane; diamino dinaphthyl 1,2 ethane; as well as the corresponding compounds substituted in the ortho, meta or other positions. Any

with good eifect to retard the deterioration of rubber and other like organic substances, preferably in moderately small proportions, say from 0.1 to per cent.

As a specific example of one embodiment of the invention of this application, a rubber com- 7 position is prepared. containing blended plantaas the control composition when subjected to an accelerated aging test such as the Geer oven test. It is to be understoodthat the term treating is employed in the appended claims in a generic sense to include either the incorporation of the anti-oxidants into the rubber or the like by mixing them into the said material while it is in a plastic or fluid condition, or by applying them to the surface of a solid mass thereof as a paste, powder or solution. The term rubber is likewise employed in the claims in a generic sense to include caoutchouc, both natural and synthetic, balata, gutta percha, rubber isomers and like products, whether or not admixed with fill-' ers, pigments, or vulcanizing or accelerating agents.

While I have herein disclosed certain preferred manners of performing my invention, I do not thereby desire or intend to limit myself solelythereto, for, as hitherto stated, the precise proportions of the materials utilized may be varied and other materials having equivalent chemical properties may be employed if desired without departing from the spirit and scope of the invention as defined in the appended claims.

This application is a continuation in part of my co-pending application Serial No. 301,423 filed August 22, 1928.

I claim:

1. The method of preserving rubber which comprises treating rubber with a substance having the general formula ARX-R'-A' wherein A and A represent amino groups which may contain hydrocarbon substituents, X represents an aliphatic nucleus, and R and R represent aromatic nuclei attached to different carbon atoms of the nucleus X.

2. The method of preserving rubber which comprises treating rubber with a substance hav ing the general formula wherein A and A represent primary amino groups, X represents an aliphatic nucleus, and

R and R represent aromatic nuclei attached to different carbon atoms of the nucleus X.

3. The method of preserving rubber which comprises treating rubber with p,p' diamino dibenzyl.

4. The method of preserving rubber which com prises treating rubber with a substance having the general formula wherein A and A represent secondary hydrocarbon substituted amino groups, X represents ATENT QFFIE 2,009,530- V T V,

. Annoxm N'r H Anthurw. Sloan; Akron, Ohio, assignor to The B. F; Goodrich Company, New corporation. of NewYork; I V I No Drawings Application May 26, 1933', Serial No. 673,117 g A-R -X-'-RA V wherein A and A represent amino groups which may contain hydrocarbon substituents, X represents an aliphatic nucleus, and R and R represent aromatic nuclei attached to different car- If bon atoms of the nucleus X.

stance having the general formula AR--XR' A' 1 v or the nucleus 'X. '7. A composition comprising rubber and'a sub wherein A and A represent primary amino groups, X represents an aliphatic nucleus, and

' Rand R represent aromatic nuclei attached to difierent carbon-atoms of the nucleus X.

, 8. A composition comprising rubber and 1 diamino' dibenzyl; Y e 9. 'A composition comprising rubber angle substance havin the general formula v A-R x-R' A" wherein A and A represent secondary hydroaliphatic nucleus, and R and Rreprese'nt am- ,carlwn-substituted. amino groups, X represents an 7 Y matic nuclei attached to difierent carbon atoms 10. A coinposition 'comprising rubber and pp 7 i, dianilino dibenzylg wlsLoAn, 

